Dispersion composition, dispersion and ink composition, and method of producing the same

ABSTRACT

There are provided a dispersion composition containing: (A) from 85 to 99.89% by weight of a dispersant (except for the following (B) and (C)); (B) from 0.01 to 5% by weight of an acetylene glycol and/or an acetylene glycol ethoxylate; and (C) from 0.1 to 10% by weight of one or two or more types selected from polyoxy (ethylene-propylene) block polymers having a weight average molecular weight of from 1,500 to 20,000, a content of ethylene oxide of from 20 to 90% by weight, and a content of propylene oxide of from 10 to 80% by weight: a dispersion and an ink composition using the same, and a method of producing the same.

CROSS-REFERENCE TO RELATED APPLICATION

This non-provisional application claims priority under 35 U.S.C. §119(a) on Patent Application No. 2018-160358 filed in Japan on Aug. 29,2018, the entire contents of which are hereby incorporated by reference.

TECHNICAL FIELD

The present invention relates to a dispersion composition, and moreparticularly, to a dispersion composition used for dispersing a dispersedye or pigment, a dispersion and an ink composition, and to a method ofproducing the same.

BACKGROUND ART

A disperse dye or pigment has hitherto been used as colorants for ink.When the disperse dye or pigment is used in ink, it is necessary todisperse a micronized disperse dye or pigment in water. However, thedisperse dye or pigment is insoluble in water, so the dispersant isimportant for rendering the disperse dye or pigment into a dispersedstate and stably maintaining that dispersed state for a prolonged periodof time. Meanwhile, in recent years, it has been desired to reduce aparticle size of the disperse dye or pigment in order to improvefineness of an image, and various dispersion methods and dispersionprocess conditions have been proposed to reduce the particle size.However, if the disperse dye or pigment is not finely and stablydispersed in a medium, an excellent transparency, fineness and colordevelopability are not obtained, and in ink for an ink jet, clogging ofnozzles is caused. However, in general, there is a practical limit tothe degree of micronization by mechanical pulverizing and dispersion ofthe disperse dye or pigment.

Heretofore, various compounds have been used as the dispersant. Forexample, in Patent Document 1, aromatic sulfonates and lignin sulfonatesare used as the dispersant for a disperse dye. In addition, in PatentDocument 2, a styrene-acrylic acid copolymer, a styrene-methacrylic acidcopolymer, a styrene-maleic acid copolymer, a sodium naphthalenesulfonate formalin condensate, or the like is used as a high molecularweight dispersant.

However, in the inks containing the disperse dye or pigment dispersionobtained by using the dispersant, the dispersant is a high molecularweight resin or surfactant, and thus the average particle size of thedisperse dye or pigment is large, and ejection stability or liquidstability is poor.

Accordingly, a method of using a plurality of dispersants has also beenattempted. For example, Patent Document 3 describes, as a dispersant,the blended use of polyoxyethylene-β-naphthyl ether, which is a nonionicsurfactant, and a sodium naphthalene sulfonate formalin condensate,which is an anionic surfactant. In addition, Patent Document 4 disclosesa pigment dispersion containing two or more selected from a sodiumnaphthalene sulfonate formalin condensate, a polycarboxylic acid graftpolymer, and polyoxyethylene styryl phenyl ether.

In addition, a method of using a dispersant and a surfactant incombination has also been attempted. For example, Patent Document 5discloses that a dispersant and two or more surfactants are used incombination. Patent Document 6 discloses a composition containing adispersant, a sulfate ester-based surfactant, and an acetyleneglycol-based surfactant having an HLB value of 6.0 or less. However, ineither case, the ability to micronize the disperse dye or pigment ispoor, and the dispersion performance has room for improvement.

CITATION LIST

Patent Document 1: JP-A 2000-239980

Patent Document 2: JP-A 2007-224210

Patent Document 3: JP-A 2008-038075

Patent Document 4: JP-A 2010-111826

Patent Document 5: JP-A 2016-060772

Patent Document 6: JP-A 2018-053035

SUMMARY OF THE INVENTION

The present invention has been made in view of the above circumstances,and it is an object of the present invention to provide a dispersioncomposition, a dispersion and an ink composition using the same, whichare capable of atomizing disperse dye or pigment and having furtherexcellent wettability and dispersion stability, and a method ofproducing the same.

As a result of intensive studies in order to achieve the above object,the inventors made the discovery that when a dispersion composition inwhich a dispersant, an acetylene glycol-based surfactant represented bythe following formula (1) and/or the following formula (2), and polyoxy(ethylene-propylene) block polymers having a specific number of addedmoles of ethylene oxide and molecular weight range are blended, is used,the disperse dye or pigment may be micronized, and further excellentwettability and dispersion stability may be obtained, and thus thepresent invention has been completed.

Therefore, the present invention provides the following dispersioncomposition, a dispersion and an ink composition using the same, and amethod of producing the same.

1. A dispersion composition comprising:

(A) from 85 to 99.89% by weight of a dispersant (except for thefollowing (B) and (C));

(B) from 0.01 to 5% by weight of an acetylene glycol represented by thefollowing formula (1) and/or an acetylene glycol ethoxylate representedby the following formula (2); and

wherein R¹ and R² each represent an alkyl group having 1 to 5 carbonatoms.

wherein R³ and R⁴ each represent an alkyl group having 1 to 5 carbonatoms, m and n are each a positive number of from 0.5 to 25, and m+n isfrom 1 to 40;

(C) 0.1 to 10% by weight of one or two or more types selected frompolyoxy (ethylene-propylene) block polymers represented by the followingformula (3) and having a weight average molecular weight of from 1,500to 20,000, a content of ethylene oxide of from 20 to 90% by weight, anda content of propylene oxide of from 10 to 80% by weight:HO(C₂H₄O)_(w)(C₃H₆O)_(w)(C₂H₄O)_(y)H  (3)wherein w, x, and y are positive numbers.2. The dispersion composition described in the above 1, wherein theweight average molecular weight of the dispersant of component (A) is100 or more.3. The dispersion composition described in the above 1, wherein in (C)the polyoxy (ethylene-propylene) block polymers, the content of ethyleneoxide is from 35 to 90% by weight, and the content of propylene oxide isfrom 10 to 65% by weight.4. The dispersion composition described in the above 1, wherein the (C)polyoxy (ethylene-propylene) block polymers have a weight averagemolecular weight of from 5,000 to 20,000.5. A dispersion comprising:

the dispersion composition described in the above 1;

a disperse dye and/or pigment; and

an aqueous solvent.

6. An ink composition comprising the dispersion described in the above5.

7. A method of producing a dispersion comprising mixing and dispersingthe dispersion composition in the above 1, a disperse dye and/orpigment, and an aqueous solvent.

8. A method of producing an ink composition, the method comprising:

obtaining a dispersion by mixing and dispersing the dispersioncomposition described in the above 1, a disperse dye and/or pigment, andan aqueous solvent; and

mixing the dispersion with at least one substance selected from thegroup consisting of water, a water-soluble organic solvent, a resin, anultraviolet absorber, an antioxidant, a pH adjuster, a preservative, anda viscosity modifier.

Advantageous Effects of the Invention

According to the dispersion composition of the present invention, thedisperse dye or pigment may be micronized. In addition, a dispersionusing this dispersion composition, and an ink composition may exhibitexcellent wettability and may exhibit dispersion stability withoutchange over time.

DESCRIPTION OF THE PREFERRED EMBODIMENT

A dispersion composition of the present invention contains:

(A) from 85 to 99.89% by weight of a dispersant (except for thefollowing (B) and (C));

(B) from 0.01 to 5% by weight of an acetylene glycol represented by thefollowing formula (1) and/or an acetylene glycol ethoxylate representedby the following formula (2); and

wherein R¹ and R² each represent an alkyl group having 1 to 5 carbonatoms.

wherein R³ and R⁴ each represent an alkyl group having 1 to 5 carbonatoms, m and n are each a positive number of from 0.5 to 25, and m+n isfrom 1 to 40;

(C) 0.1 to 10% by weight of one or two or more selected from polyoxy(ethylene-propylene) block polymers represented by the following formula(3) and having a weight average molecular weight of from 1,500 to20,000, a content of ethylene oxide of from 20 to 90% by weight, and acontent of a propylene oxide of from 10 to 80% by weight:HO(C₂H₄O)_(w)(C₃H₆O)_(w)(C₂H₄O)_(y)H  (3)wherein w, x, and y are positive numbers.

The dispersant of component (A) is not particularly limited as long asit is a known dispersant except for the following (B) and (C). Examplesthereof can include a high molecular weight dispersant, a low molecularweight surfactant, or the like. However, it is preferable to use thecompound having a molecular weight (weight average molecular weight) of100 or more and it is preferable to use a high molecular weightdispersant in view of storage stability of the ink. The term “lowmolecule” refers to a molecule (weight average molecular weight) havinga molecular weight of 1,000 or less, and preferably 100 or more. Theterm “high molecule” refers to a molecule having a molecular weight(weight average molecular weight) exceeding 1,000, and preferably a highmolecular weight dispersant having a molecular weight of from 3,000 to20,000. The above molecular weight (weight average molecular weight) ismeasured in conformity to JIS K 7252. In the present invention, thedispersant preferably having weight average molecular weight of theabove numeral range may be used.

Examples of the high molecular weight dispersant can include naturalgums such as gum arabic and tragacanth gum, glucosides such as saponin,cellulose derivatives such as methylcellulose, carboxycellulose, andhydroxymethylcellulose, lignin sulfonate (Na, K, Ca, Mg) or a formalincondensate thereof, natural polymers such as shellac, anionic polymerssuch as polyacrylates, styrene-anhydride maleic copolymer,olefin-anhydride maleic copolymer, polystyrene sulfonate (Na, K),acrylamide-acrylic acid copolymer, sodium alginate, salts ofstyrene-acrylic acid copolymer, salts of vinyl naphthalene-maleic acidcopolymer, salts of naphthalene sulfonic acid formalin condensates, ornonionic polymers such as polyvinyl alcohol, polyalkylene polyamines,poly acrylamide, polyvinyl pyrrolidone, and polyethylene glycol.

More preferably, that can include cellulose derivatives such asmethylcellulose, carboxycellulose and hydroxymethylcellulose, ligninsulfonate (Na, K) or a formalin condensates, natural polymers such asshellac, polyacrylate (Na, K), styrene-anhydride maleic acid copolymer,olefin-anhydride maleic copolymer, polystyrene sulfonate (Na, K),acrylamide-acrylic acid copolymer, sodium alginate, salts ofstyrene-acrylic acid copolymer (Na, K), salts of vinylnaphthalene-maleic acid copolymer (Na, K), salts of naphthalene sulfonicacid formalin condensate (Na, K), polyvinyl alcohol, polyalkylenepolyamines, polyacrylamide, polyvinyl pyrrolidone, or polyethyleneglycol.

In addition, examples of the low molecular weight surfactant can includeanionic surfactants such as

carboxylate types such as carboxylate, ether carboxylate, acyl aminoacid salt, etc.,

sulfate ester types such as sulfate ester salt, ether sulfate estersalt, amide ether sulfate ester salt, etc.,

sulfonate types such as sulfonate, sulfosuccinate, acyl taurate,isethionate, etc.,

phosphate ester salt types such as alkyl monophosphate Na salt,alkyltriphosphate Na salt, polyoxyethylene alkyl ether phosphate estersalt, di (tri) polyoxyethylene alkyl ether phosphate ester Na salt,tripolyoxyethylene alkyl ether phosphate, etc.,

or nonionic surfactants such as

oxyethylene chain types such as ether type, ether ester type,oxyethylene chain-oxypropylene chain addition type,ethylenediamine-oxypropylene chain-oxyethylene chain addition type,hydroxyl group-containing types such as sorbitan ester, glyceride, alkylfatty acid (mono, poly) ester of polyglycerin, polyglycerin condensedricinoleate ester, organic acid monoglyceride, propylene glycol fattyacid ester, sucrose fatty acid esters, alkyl glyceryl ethers, alkylpolyglucosides, lecithin.Each of these compounds may also be appropriately selected and one ortwo or more thereof may be used.

The blended amount of component (A) is from 85 to 99.89% by weight, andpreferably from 90 to 99.8% by weight, per the total of the dispersioncomposition as an active ingredient. If the blended amount of component(A) is less than 85% by weight, dispersion failure of the disperse dyeoccurs, and if the blended amount of component (A) exceeds 99.89% byweight, generation of bubbles is increased.

Component (B) of the dispersion composition of the present invention isone or two or more of acetylene glycols selected from an acetyleneglycol represented by the following formula (1) and/or an acetyleneglycol ethoxylate represented by the following formula (2):

wherein R¹ and R² each represent an alkyl group having 1 to 5 carbonatoms.

wherein R³ and R⁴ each represent an alkyl group having 1 to 5 carbonatoms, m and n are each a positive number of from 0.5 to 25, and m+n isfrom 1 to 40.

Here, the total number of added moles of ethylene oxide in theethoxylate represented by formula (2) is from 1 to 40 moles, andpreferably from 2 to 12 moles. If the total number of added moles ofethylene oxide exceeds 40 moles, the static and dynamic surface tensionof the ink composition is increased.

These acetylene glycols which are component (B) can be used alone or incombination of two or more, and the amount used in producing thedispersion composition of the present invention is from 0.01 to 5% byweight, and preferably from 0.1 to 1% by weight. If the amount ofacetylene glycols is less than 0.01% by weight, the dynamic surfacetension is increased, which causes cissing at the time of high-speedprinting. If the amount of acetylene glycols exceeds 5% by weight, thesolubility in water is deteriorated, such that aggregates are generatedat the time of blending, and the effect of reducing the surface tensioncannot be obtained, resulting in cissing or remarkably deterioratedstability at a low temperature, which makes blending difficult.

The polyoxy (ethylene-propylene) block polymers of component (C) arerepresented by the following formula (3):HO(C₂H₄O)_(w)(C₃H₆O)_(w)(C₂H₄O)_(y)H  (3),wherein w, x, y are positive numbers. w+y is preferably from 10 to 200,and x is preferably from 10 to 50. Specifically, for example, thefollowing compounds can be included, and these may be used alone or incombination of two or more:HO(C₂H₄O)_(w)(C₃H₆O)₂₀(C₂H₄O)_(y)H (where w+y=27),HO(C₂H₄O)_(w)(C₃H₆O)₃₀(C₂H₄O)_(y)H (where w+y=160),HO(C₂H₄O)_(w)(C₃H₆O)₃₅(C₂H₄O)_(y)H (where w+y=30),HO(C₂H₄O)_(w)(C₃H₆O)₃₅(C₂H₄O)_(y)H (where w+y=48),HO(C₂H₄O)_(w)(C₃H₆O)₂₀(C₂H₄O)_(y)H (where w+y=155).

In addition, the weight average molecular weight of component (C) isfrom 1,500 to 20,000, and particularly preferably from 5,000 to 20,000.If the weight average molecular weight of component (C) is less than1,500, since a solubilization ability is reduced and the solubility inwater is reduced, insoluble materials are generated upon blending withink. If the weight average molecular weight of component (C) exceeds20,000, the dynamic surface tension is large, which causes bleeding atthe time of printing. In addition, the weight average molecular weightis a value measured by gel permeation chromatography (GPC).

In addition, the content of ethylene oxide is from 20 to 90% by weight,and particularly preferably from 35 to 90% by weight. If the content ofethylene oxide is less than 20% by weight, the solubilization ability isreduced and aggregates are generated. If the content of ethylene oxideexceeds 90% by weight, the solubilization ability is increased, but thedynamic surface tension is increased, resulting in cissing at the timeof high speed coating.

The content of propylene oxide is also from 10 to 80% by weight, andmore preferably from 10 to 65% by weight. It is more preferable that thecontent of ethylene oxide is higher than that of propylene oxide.

The amount of component (C) used in producing the dispersion compositionof the present invention is from 0.1 to 10% by weight, and preferablyfrom 0.5 to 5% by weight. If the amount of component (C) is less than0.1% by weight, sufficient solubilization of component (B) is notachieved and water solubility is lowered, resulting in aggregates uponblending. If the amount of component (C) exceeds 10% by weight, uponblending, a lot of bubbles are generated or dynamic surface tension isincreased, resulting in unevenness of coating or cissing.

The dispersion composition of the present invention contains components(A), (B), and (C), and has a composition of (A)+(B)+(C)=100% by weight.

The dispersion of the present invention contains the dispersioncomposition as described above, a disperse dye and/or pigment, and anaqueous solvent, and is particularly preferably used as an inkcomposition.

The constituent ingredients of the dispersion are described below.

In the dispersion of the present invention, the blended amount of thedispersion composition is preferably from 1 to 100 parts by weight, morepreferably from 10 to 90 parts by weight, and further preferably from 30to 80 parts by weight, per 100 parts by weight of the disperse dye andpigment as an active ingredient. If the blended amount of the dispersingcomposition is too small, the disperse dye or pigment cannot besufficiently dispersed. In addition, if the blended amount of thedispersion composition is too large, a large amount of the dispersantnot adsorbed to the disperse dye or pigment is present in thedispersion, which is not preferable.

Known disperse dyes can be used without particular limitation as thedisperse dye. The disperse dyes are compounds which are classified bychemical structures, such as benzene azo structures (monoazo, disazo),heterocyclic azo structures (thiazole azo, benzothiazole azo, pyridoneazo, pyrazolone azo, thiophene azo, etc.), anthraquinone structures, andcondensed structures (quinophthalone, styryl, coumarin, etc.), and whichhave characteristics such as a poor solubility in water because theylack water-soluble groups and have a molecular weight of 2,000 or less,which is small compared to other dyes.

Examples of disperse dyes that can be preferably used in the presentinvention include the following:

yellow dyes such as C. I. Disperse Yellow 3, 4, 5, 7, 9, 13, 24, 30, 33,34, 42, 44, 49, 50, 51, 54, 56, 58, 60, 63, 64, 66, 68, 71, 74, 76, 79,82, 83, 85, 86, 88, 90, 91, 93, 98, 99, 100, 104, 114, 116, 118, 119,122, 124, 126, 135, 140, 141, 149, 160, 162, 163, 164, 165, 179, 180,182, 183, 186, 192, 198, 199, 202, 204, 210, 211, 215, 216, 218, and224;

orange dyes such as C. I. Disperse Orange 1, 3, 5, 7, 11, 13, 17, 20,21, 25, 29, 30, 31, 32, 33, 37, 38, 42, 43, 44, 45, 47, 48, 49, 50, 53,54, 55, 56, 57, 58, 59, 61, 66, 71, 73, 76, 78, 80, 89, 90, 91, 93, 96,97, 119, 127, 130, 139, and 142;

red dyes such as C. I. Disperse Red 1, 4, 5, 7, 11, 12, 13, 15, 17, 27,43, 44, 50, 52, 53, 54, 55, 56, 58, 59, 60, 65, 72, 73, 74, 75, 76, 78,81, 82, 86, 88, 90, 91, 92, 93, 96, 103, 105, 106, 107, 108, 110, 111,113, 117, 118, 121, 122, 126, 127, 128, 131, 132, 134, 135, 137, 143,145, 146, 151, 152, 153, 154, 157, 159, 164, 167, 169, 177, 179, 181,183, 184, 185, 188, 189, 190, 191, 192, 200, 201, 202, 203, 205, 206,207, 210, 221, 224, 225, 227, 229, 239, 240, 257, 258, 277, 278, 279,281, 288, 289, 298, 302, 303, 310, 311, 312, 320, 324, and 328;

violet dyes such as C. I. Disperse Violet 1, 4, 8, 23, 26, 27, 28, 31,33, 35, 36, 38, 40, 43, 46, 48, 50, 51, 52, 56, 57, 59, 61, 63, 69, and77;

green dyes such as C. I. Disperse Green 6:1, and 9;

brown dyes such as C. I. Disperse Brown 1, 2, 4, 9, 13, 19, and 27;

blue dyes such as C. I. Disperse Blue 3, 7, 9, 14, 16, 19, 20, 26, 27,35, 43, 44, 54, 55, 56, 58, 60, 62, 64, 71, 72, 73, 75, 79, 81, 82, 83,87, 91, 93, 94, 95, 96, 102, 106, 108, 112, 113, 115, 118, 120, 122,125, 128, 130, 139, 141, 142, 143, 146, 148, 149, 153, 154, 158, 165,167, 171, 173, 174, 176, 181, 183, 185, 186, 187, 189, 197, 198, 200,201, 205, 207, 211, 214, 224, 225, 257, 259, 267, 268, 270, 284, 285,287, 288, 291, 293, 295, 297, 301, 315, 330, 333, 359, and 360; and

black dyes such as C.I. Disperse Black 1, 3, 10, and 24.

Dyes available from Nippon Kayaku Co., Ltd. that can be preferably usedinclude Kayaset Black K-R, A-N, Kayalon Polyester Black S-200, EX-SF300, G-SF, BR-SF, 2B-SF 200, TA-SF 200, AUL-S, Kayaset Yellow K-CL,Kayalon Polyester Yellow 4G-E, Kayalon Polyester Light Yellow 5G-S,Kayaset Red K-BL, Kayacelon Red E-BF, SMS-5, SMS-12, Kayalon PolyesterRed TL-SF, BR-S, BL-E, HL-SF, 3BL-5200, AUL-S, Kayalon Polyester LightRed B-5200, Kayalon Polyester Rubine BL-5200, Kayaset Blue N, K-FL,MSB-13, Kayalon Polyester Blue BR-SF, T-S, Kayalon Polyester Light BlueBGL-5200, Kayalon Polyester Turq Blue GL-5200, Kayalon Polyester BlueGreen FCT-S, or the like.

Dyes available from Orient Chemical Industries Co., Ltd. that can bepreferably used include Valifast Black 3806, 3810, 3820, Oil Black BS,BY, B-85, 860, Water Yellow 6C, Valifast Yellow 1101, 1105, 3110, 3120,4120, 4126, Oplas Yellow 130, 140, Oil Yellow GG-S, 105, 107, 129, 818,Water Red 27, Valifast Red 1306, 1355, 2303, 3311, 3320, Valifast Orange3210, Valifast Brown 2402, Oil Red 5B, Oil Pink 312, Oil Brown BB,Valifast Blue 1601, 1603, 1605, 2606, 3806, 3820, Oil Blue #15, #613,613, N14, BOS, or the like.

Dyes available from Sumitomo Chemical Co., Ltd. that can be preferablyused include Sumikaron Black S-BL, S-BF extra conc., S-RPD, S-XE 300%,Sumikaron Yellow SE-4G, SE-5G, SE-3GL conc., SE-RPD, Sumikaron BrilliantFlavine S-10G, Sumikaron Red E-FBL, E-RPD(E), S-RPD(S), SumikaronBrilliant Red S-BF, S-BLF, SE-BL, SE-BGL, SE-2BF, SE-3BL(N), SumikaronRed E-FBL, E-RPD(E), S-RPD(S), Sumikaron Brilliant Red S-BF, S-BLF,SE-BL, SE-BGL, SE-2BF, SE-3BL(N), Sumikaron Brilliant Blue S-BL,Sumikaron Turquoise Blue S-GL, S-GLFgrain, or the like.

Dyes available from BASF that can be preferably used include BasacrylBlack X-BGW, NaozaponBlack X-51, X-55, Neozapon Yellow 081, LurafixYellow 138, or the like, Zapon Blue 807, Neozapon Blue 807, LurafixBlue590, 660, Orasol Black RLI, RL, CN, Oracet Yellow 8GF, GHS, OrasolRed G, Oracet Pink RP, Orasol Blue GL, GN, 2R, or the like.

Dyes available from Taoka Chemical Company, Limited that can bepreferably used include Oleosol Fast Black AR, RL, Oleosol Fast Pink FB,Rhodamine A, B, B gran., Oleosol Fast Yellow 2G, Oleosol Fast Blue ELN,or the like.

Dyes available from Hodogaya Chemical Co., Ltd. that can be preferablyused include Spilon Black BNH, MH special, or the like.

Dyes available from Mitsui Chemicals, Incorporated that can bepreferably used include PS Yellow GG, MS Yellow HD-180, PS Red G, MSMagenta VP, or the like.

Dyes available from Bayer AG that can be preferably used include CeresBlue GN 01, or the like.

Dyes available from Sumika Color Co., Ltd. that can be preferably usedinclude TS Yellow 118 cake, ESC Yellow 155, Sumiplast Yellow HLR, GC, TSTurq Blue 618, 606, ESC Blue 655, 660, Sumiplast BlueS, OA, or the like.

Known pigments can be used without particular limitation as the pigment.Examples of organic pigments can include azo pigments such as solubleazo pigments, insoluble azo pigments, and condensed azo pigments;polycyclic pigments such as quinacridone pigments, perylene pigments,perinone pigments, isoindolinone pigments, isoindoline pigments,dioxazine pigments, thioindigo pigments, anthraquinone pigments,quinophthalone pigments, metal complex pigments, anddiketo-pyrrolo-pyrrole pigments; and phthalocyanine pigments. Inaddition, examples of inorganic pigments can include carbon black, metaloxides, metal hydroxides, metal sulfides, metal ferrocyanides, metalchlorides, or the like. In addition, examples of carbon blacks caninclude furnace black, lamp black, acetylene black, channel black, orthe like.

Specific examples of pigments can include red pigments such as C.I.Pigment Red 7, 9, 14, 41, 48:1, 48:2, 48:3, 48:4, 81:1, 81:2, 81:3, 122,123, 146, 149, 168, 177, 178, 179, 187, 200, 202, 208, 210, 215, 224,254, 255, and 264;

yellow pigments such as C.I. Pigment Yellow 1, 3, 5, 6, 14, 55, 60, 61,62, 63, 65, 73, 74, 77, 81, 93, 97, 98, 104, 108, 110, 128, 138, 139,147, 150, 151, 154, 155, 166, 167, 168, 170, 180, 188, 193, 194, and213;

orange pigments such as C. I. Pigment Orange 36, 38, and 43;

blue pigments such as C. I. Pigment Blue 15, 15:2, 15:3, 15:4, 15:6, 16,22, and 60;

green pigments such as C.I. Pigment Green 7, 36, and 58;

violet pigments such as C.I. Pigment Violet 19, 23, 32, and 50; and

black pigments such as C.I. Pigment Black 7.

Of these, preferred use can be made of, for example, C.I. Pigment Red122, C.I. Pigment Yellow 74, 128 and 155, C.I. Pigment Blue 15:3, 15:4and 15:6, C.I. Pigment Green 7 and 36, C.I. Pigment Violet 19, and C.I.Pigment Black 7.

With regard to the disperse dye and/or pigment included in thedispersion, the type, particle size, treatment method and the like maybe suitably selected according to the intended purpose thereof. Inaddition, the disperse dye and pigment included in the dispersion may beused alone or in combination of two or more.

The concentration of the disperse dye and pigment in the dispersion ispreferably from 1 to 50% by weight, and more preferably from 5 to 40% byweight, per 100% by weight of the dispersion. If the concentration ofthe disperse dye and pigment exceeds 50% by weight, the density of thedisperse dye and pigment in the dispersion is increased, such that freemovement is disturbed. Thus, there is a possibility of aggregation.

Water and/or a water-soluble organic solvent may be used as the aqueoussolvent, and two or more such solvent may be used in admixture. Thewater is preferably pure water or ion exchange water (deionized water).In addition, examples of water-soluble organic solvents that may be usedinclude alcohols such as methyl alcohol, ethyl alcohol, n-propylalcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, andtert-butyl alcohol; glycols such as ethylene glycol, propylene glycol,dipropylene glycol, butylene glycol, triethylene glycol,1,2,6-hexanetriol, thiodiglycol, hexylene glycol, and diethylene glycol;glycol ethers such as ethylene glycol monomethyl ether, ethylene glycolmonoethyl ether, diethylene glycol methyl ether, diethylene glycol ethylether, triethylene glycol monomethyl ether, triethylene glycol monoethylether, and triethylene glycol monobutyl ether; polyhydric alcohols suchas glycerol; and nitrogen-containing compounds such asN-methyl-2-pyrrolidone, 2-pyrrolidone, and1,3-dimethyl-2-imidazolidinone. In addition, in a case where a mixedsolution of water and a water-soluble organic solvent is used, the ratioof the water-soluble organic solvents is 10% by weight or less,preferably from 0.01 to 5% by weight, per 100% by weight of thedispersion.

The ratio of water and a water-soluble organic solvent in the dispersionis preferably from 5 to 95% by weight, and more preferably from 30 to90% by weight, per 100% by weight of the dispersion.

The method of producing the dispersion of the present inventionpreferably includes in particular mixing and dispersing theabove-described dispersion composition, disperse dye and/or pigment, andaqueous solvent. For example, the dispersion can be obtained by mixingthe dispersant with the disperse dye and/or pigment, and the aqueoussolvent using a mixing and dispersing apparatus such as a paint shaker,bead mill, ball mill, dissolver, and kneader. Moreover, in case whereingredients that are solid at room temperature are used, they may beheated and mixed if necessary.

The dispersion has a viscosity of preferably 10.0 mPa·s or less, andmore preferably 5.0 mPa·s or less. In addition, it is desirable for thelower limit in the viscosity of the dispersion to be at least 1.0 mPa·s.Here, the viscosity is measured at 25° C.

The average particle size of the disperse dye and/or pigment in thedispersion has, for example, 330 nm or less, and preferably from 100 to300 nm, as the particle size after 5 hours of dispersion in thedispersion. “Average particle size” here refers to the median diameter(D50).

The static surface tension of the dispersion is preferably 50 mN/m orless, and more preferably 45 mN/m or less, and the lower limit is morepreferably 20 mN/m or more.

In addition, the ink composition of the present invention preferablycontains (i) to (iii) below:

(i) a dispersion composition,

(ii) a disperse dye and/or pigment, and

(iii) a water and/or water-soluble organic solvent.

Furthermore, it is preferable to optionally add additives such asresins, ultraviolet absorbers, antioxidants, pH adjusters,preservatives, and viscosity modifiers.

The concentration of the disperse dye and/or pigment in the inkcomposition is preferably from 0.1 to 20% by weight, and more preferablyfrom 0.1 to 10% by weight, per 100% by weight of the ink composition.

The ratio of water and/or the water-soluble organic solvent in the inkcomposition is preferably from 50 to 99% by weight, and more preferablyfrom 60 to 95% by weight, per 100% by weight of the ink composition.

The resin contained in the ink composition is preferably a polymerhaving hydrophobic groups and hydrophilic groups. Such a polymerpreferably has at least one functional group selected from alkyl groups,cycloalkyl groups and aryl groups, as hydrophobic groups. In addition,such a polymer preferably has at least one functional group selectedfrom carboxyl groups, sulfo groups, hydroxyl groups, amino groups, amidegroups, and functional groups thereof, as hydrophilic groups. Such apolymer can be obtained by polymerizing monomers or oligomers havingfunctional groups such as acryloyl, methacryloyl, vinyl, and allylgroups. Specifically, examples of such monomers and oligomers that maybe used include styrene, tetrahydrofurfuryl acrylate, butylmethacrylate, (α, 2, 3 or 4)-alkylstyrene, (α, 2, 3 or 4)-alkoxystyrene,3,4-dimethylstyrene, α-phenylstyrene, divinylbenzene, vinylnaphthalene,dimethylamino (meth)acrylate, dimethylaminoethyl (meth)acrylate,dimethylaminopropyl acrylamide, N,N-dimethylaminoethyl acrylate,acryloyl morpholine, N,N-dimethyl acrylamide, N-isopropyl acrylamide,N,N-diethyl acrylamide, methyl (meth)acrylate, ethyl (meth)acrylate,propyl (meth)acrylate, ethylhexyl (meth)acrylate and other alkyl(meth)acrylate, methoxydiethylene glycol (meth)acrylate, (meth)acrylatesof diethylene glycol or polyethylene glycol with ethoxy, propoxy orbutoxy groups, cyclohexyl (meth)acrylate, benzyl (meth)acrylate,phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate and hydroxyalkyl(meth)acrylates; and other (mono, di, tri, tetra or poly)ethylene glycoldi(meth)acrylates in cases where a crosslinked structure is to beintroduced in addition to the single function such as fluorine, chlorineor silicon-containing (meth)acrylates, (meth)acrylamide, maleic acidamide, (meth)acrylate; (meth)acrylate such as 1,4-butanediol,1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol and 1,10-decanediol,trimethylolpropane tri(meth)acrylate, glycerol (di or tri)(meth)acrylate, di(meth)acrylates of ethylene oxide adducts of bisphenolA or F; and an acrylic or methacrylic group-containing compounds such asneopentyl glycol di(meth)acrylate, pentaerythritol tetra(meth)acrylateand dipentaerythritol hexa(meth)acrylate.

The ratio of resin in the ink composition is not particularly limited,but preferably from 0 to 30% by weight, and more preferably from 0 to20% by weight, per 100% by weight of the ink composition. In addition,in a case where a resin is blended in the ink composition, the amountthereof is preferably set to at least 1% by weight.

In addition, various additives can be contained in the ink composition.Examples of additives can include ultraviolet absorbers, antioxidants,pH adjustors, preservatives, viscosity modifiers, or the like. These maybe suitably selected and blended in the ink composition. These additivescan be blended within the balance of the 100% by weight of thedispersion and ink composition, aside from the disperse dye and/orpigment, the water and/or water-soluble organic solvent, and the resin,and specifically in a ratio of from 0 to 10% by weight per 100% byweight of the ink composition.

In addition, the method of producing the ink composition is notparticularly limited, but it is preferable to adopt a method includingobtaining a dispersion by mixing and dispersing the above-describeddispersant, disperse dye and/or pigment, and aqueous solvent; and mixingthe dispersion with at least one substance selected from the groupconsisting of water, water-soluble organic solvents, resins, ultravioletabsorbers, antioxidants, pH adjustors, preservatives, and viscositymodifiers.

The ink composition is applied onto a recording medium by an inkjetrecording method, a recording method involving the use of a writingimplement such as a pen, and some other printing method. It isespecially preferable to use the ink composition of the presentinvention in an inkjet recording method.

EXAMPLES

The present invention will hereinafter be described in detail withreference to Examples and Comparative Examples, but the presentinvention is not limited thereto. In addition, in the followingExamples, “parts” and “%” indicate “parts by weight” and “% by weight”,respectively.

Example 1

A plastic vessel (made of polypropylene and having a capacity of 0.5 L)was charged with 15 parts of the red disperse dye DR-60 (C.I. DisperseRed 60), 74.7 parts of ion-exchanged water as an aqueous solvent, and0.1 part of propylene glycol, 10.0 parts of compound (A-1) as component(A) 0.0.05 parts of compound (B-1) as component (B), 0.15 parts ofcompound (C-1) as component (C), and 300 parts of zirconia beads(diameter 0.3 mm), and dispersed for 1 hour, 3 hours and 5 hours usingPAINT SHAKER (manufactured by Asada Iron Works, Co. Ltd.). Followingdispersing, the zirconia beads were filtered off to obtain a dispersion.

Examples 2 to 18 and Comparative Examples 1 to 11

A dispersion having the composition shown in Tables 1, 2, and 3 wereprepared in the same method as in Example 1.

The viscosity, average particle size, and surface tension for eachdispersion were measured by the following methods. The results are shownin Tables 1, 2, and 3 below. In addition, in each table, parenthesesindicate the amount of active ingredient. The active ingredient of eachcomponent which is not described in parentheses is 100%, and each partby weight shows the amount of the active ingredient.

<Viscosity>

The viscosity (at 25° C.) of the dispersion after 1 hour, 3 hours, and 5hours of dispersion was measured using a TVE-20 E-type viscometer(manufactured by Toki Sangyo Co., Ltd.). It is desirable for theviscosity to be constant even if the dispersion time is long.

<Average Particle Size>

The average particle size (D50) of the disperse dye at each dispersiontime was measured as in the viscosity using a concentrated particle sizeanalyzer FPAR-1000 (manufactured by Otsuka Electronics Co., Ltd.).

<Surface Tension>

The static surface tension of the dispersion at each dispersion time wasmeasured as in the viscosity using a DY-500 high-performance surfacetensiometer (manufactured by Kyowa Interface Science, Inc.). It isdesirable for the static surface tension to be maintainable even if thedispersion time is long.

TABLE 1 Example 1 2 3 4 5 6 7 8 A A-1 10.0 10.0 10.0 10.0 10.0 10.0 10.010.0 (pbw) A-2 A-3 A-4 A-5 A-6 B B-1 0.05 0.05 0.05 0.05 0.05 0.05 0.050.05 (pbw) B-2 B-3 C C-1 0.15 0.15 0.15 0.15 0.15 (pbw) C-2 0.15 C-30.15 C-4 0.15 C-5 Disperse dye DR-60 15.0 15.0 15.0 15.0 (pbw) DY-5415.0 DB-359 15.0 DB-360 15.0 DBr-27 15.0 Aqueous Propylene glycol 0.100.10 0.10 0.10 0.10 0.10 0.10 0.10 solvent Water 74.70 74.70 74.70 74.7074.70 74.70 74.70 74.70 Viscosity 1 hour 4.4 4.1 4.6 4.5 4.3 4.4 4.6 4.5(mPa · s) 3 hours 4.5 4.2 4.7 4.5 4.1 4.3 4.8 4.7 5 hours 4.5 4.0 4.64.7 4.1 4.5 4.9 4.7 Average 1 hour 556 763 613 663 503 716 678 412particle size 3 hours 321 543 396 374 364 512 499 299 (nm) 5 hours 210275 241 209 247 302 297 187 Surface 1 hour 38.6 38.1 39.9 40.3 41.8 39.839.1 40.5 tension 3 hours 38.9 38.6 39.8 40.7 41.3 40.3 40.3 40.9 (mN/m)5 hours 40.1 38.4 39.8 40.9 41.1 40.9 41.1 41.8

TABLE 2 Example 9 10 11 12 13 14 15 16 17 18 A A-1 10.0 10.0 10.0 15.0(pbw) A-2 10.0 A-3 10.0 A-4 40.0 (8.0) A-5 20.0 (8.0) A-6 20.0 (8.0) A-71.50 B B-1 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 (pbw) B-2 0.08 B-30.02 C C-1 0.18 0.20 0.15 0.15 0.15 0.15 0.15 0.15 0.15 (pbw) C-2 C-3C-4 C-5 0.15 Disperse DR-60 15.0 15.0 15.0 15.0 15.0 15.0 15.0 15.0 15.025.0 dye DY-54 (pbw) DB-359 DB-360 DBr-27 Aqueous Propylene 0.10 0.100.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 solvent glycol Water 74.70 74.6474.68 74.70 74.70 44.70 64.70 64.70 83.20 59.70 Viscosity 1 hour 4.6 4.54.3 4.5 4.1 4.8 4.3 4.6 1.8 9.9 (mPa · s) 3 hours 4.6 4.8 4.6 4.5 4.24.7 4.2 4.5 1.8 9.9 5 hours 4.6 4.6 4.5 4.6 4.3 4.7 4.2 4.4 1.8 10.2Average 1 hour 426 722 778 455 432 698 632 656 660 597 particle 3 hours287 517 569 301 311 461 399 378 215 301 size 5 hours 194 298 277 189 191236 241 263 153 222 (nm) Surface 1 hour 40.9 42.3 43.2 40.5 42.3 38.139.1 39.0 34.0 40.2 tension 3 hours 40.4 43.0 44.4 41.1 42.9 38.3 39.539.0 34.9 40.5 (mN/m) 5 hours 41.6 43.1 44.9 41.2 43.0 38.6 39.9 39.635.5 40.9

TABLE 3 Comparative Example 1 2 3 4 5 6 7 8 9 10 11 A A-1 10.0 10.0 10.010.0 10.0 10.0 10.0 10.0 (pbw) A-2 30.0 (6.0) A-3 20.0 (8.0) A-4 20.0(8.0) B B-1 0.50 (pbw) B-2 0.75 B-3 C C-1 0.50 0.05 (pbw) C-2 C-3 C-4C-5 Disperse dye DR-60 15.0 15.0 15.0 15.0 15.0 15.0 15.0 (pbw) DY-5415.0 DB-359 15.0 DB-360 15.0 DBr-27 15.0 Aqueous Propylene 0.1 solventglycol Water 74.90 75.00 75.00 75.00 75.00 55.00 65.00 65.00 74.50 74.5074.20 Viscosity 1 hour 4.5 4.3 4.7 4.6 4.3 4.3 4.2 4.6 4.9 4.5 4.8 (mPa· s) 3 hours 4.6 4.2 4.7 4.6 4.3 4.1 4.2 4.5 5.0 4.6 4.8 5 hours 4.5 4.34.7 4.9 4.3 4.1 4.2 4.4 5.2 4.7 4.8 Average 1 hour 1,014 1,546 1,3241,444 1,234 1,366 1,293 1,542 793 687 811 particle size 3 hours 743 879899 917 793 999 893 911 562 482 555 (nm) 5 hours 598 711 618 643 619 736687 794 425 350 439 Surface 1 hour 47.9 49.9 47.6 48.9 50.1 50.9 50.048.7 37.9 40.1 38.9 tension 3 hours 48.5 50.1 47.9 48.1 50.3 51.0 49.849.1 38.2 40.3 39.0 (mN/m) 5 hours 49.9 50.6 47.8 47.9 50.7 51.3 50.349.0 38.8 40.5 39.6

In Tables 1 to 3, details of the components (A), (B) and (C) in eachtable are as follows:

(A-1): sodium lignin sulfonate

(manufactured by West Virginia Pulp & Paper Company,

-   -   weight average molecular weight: 8,400)        (A-2): sodium lignin sulfonate

(PEARLLEX NP manufactured by Nippon Paper Industries Co., Ltd.,

-   -   weight average molecular weight: 12,000)        (A-3): modified sodium lignin sulfonate

(PEARLLEX DP manufactured by Nippon Paper Industries Co., Ltd.,

-   -   weight average molecular weight: 12,000)        (A-4): SMA-1440

(manufactured by KAWAHARA PETROCHEMICAL CO., LTD.,

-   -   active ingredient: 20%, styrene⋅maleic anhydride copolymer,    -   weight average molecular weight: 7,000)        (A-5): SHALLOL AN-103P

(manufactured by DKS Co. Ltd.,

-   -   active ingredient: 40%, sodium polyacrylate,    -   weight average molecular weight: 10,000)        (A-6): LAVELIN FD-40

(manufactured by DKS Co. Ltd.,

-   -   active ingredient: 40%, a sodium naphthalene sulfonate formalin        condensate,    -   weight average molecular weight: 4,000)        (A-7): Noigen EA-137

(manufactured by DKS Co. Ltd.,

-   -   active ingredient: 100%, polyoxyethylene styryl phenyl ether    -   weight average molecular weight: from 850 to 950)        (B-1): 2,5,8,11-tetramethyl-6-dodecyne-5,8-diol ethoxylate

(In formula (2), the average value of m+n=4.)

(B-2): 2,4,7,9-tetramethyl-5-decyne-4,7-diol ethoxylate

(In formula (2), the average value of m+n=4)

(B-3): 2,4,7,9-tetramethyl-5-decyne-4,7-diol

(C-1): In formula (3), w+y=48, weight average molecular weight: 5,250,

content of ethylene oxide: 40%, content of propylene oxide: 60%

(C-2): In formula (3), w+y=12, weight average molecular weight: 1,800,

content of ethylene oxide: 30%, content of propylene oxide: 70%

(C-3): In formula (3), w+y=26, weight average molecular weight: 2,900,

content of ethylene oxide: 40%, content of propylene oxide: 60%

(C-4): In formula (3), w+y=145, weight average molecular weight: 8,000,

content of ethylene oxide: 80%, content of propylene oxide: 20%

(C-5): In formula (3), w+y=205, weight average molecular weight: 11,250,

content of ethylene oxide: 80%, content of propylene oxide: 20%

(DR-60): C. I. Disperse Red 60

(DY-54): C. I. Disperse Yellow 54

(DB-359): C. I. Disperse Blue 359

(DB-360): C. I. Disperse Blue 360

(DBr-27): C. I. Disperse Brown 27

Japanese Patent Application No. 2018-160358 is incorporated herein byreference.

Although some preferred embodiments have been described, manymodifications and variations may be made thereto in light of the aboveteachings. It is therefore to be understood that the invention may bepracticed otherwise than as specifically described without departingfrom the scope of the appended claims.

The invention claimed is:
 1. A dispersion composition consisting of: (A)from 85 to 99.89% by weight of a dispersant (except for the following(B) and (C)); (B) from 0.01 to 5% by weight of an acetylene glycolrepresented by the following formula (1) and/or an acetylene glycolethoxylate represented by the following formula (2); and

wherein R¹ and R² each represent an alkyl group having 1 to 5 carbonatoms;

wherein R³ and R⁴ each represent an alkyl group having 1 to 5 carbonatoms, m and n are each a positive number of from 0.5 to 25, and m+n isfrom 1 to 40; (C) from 0.1 to 10% by weight of one or two or more typesselected from polyoxy (ethylene-propylene) block polymers represented bythe following formula (3) and having a weight average molecular weightof from 1,500 to 20,000, a content of ethylene oxide of from 20 to 90%by weight, and a content of propylene oxide of from 10 to 80% by weight:HO(C₂H₄O)_(w)(C₃H₆O)_(x)(C₂H₄O)_(y)H  (3) wherein w, x, and y arepositive numbers, and wherein said dispersant (A) consists of at leastone of: a high molecular weight dispersant having a weight averagemolecular weight exceeding 1,000; a low molecular weight anionicsurfactant having a weight average molecular weight of 1,000 or less;and a low molecular weight nonionic surfactant having a weight averagemolecular weight of 1,000 or less, the high molecular weight dispersantbeing selected from the group consisting of methylcellulose,carboxycellulose, hydroxymethylcellulose, lignin sulfonate (Na, K), aformalin condensate of lignin sulfonate (Na, K), shellac, polyacrylate(Na, K), a styrene-anhydride maleic acid copolymer, an olefin-anhydridemaleic copolymer, polystyrene sulfonate (Na, K), an acrylamide-acrylicacid copolymer, sodium alginate, a salt of styrene-acrylic acidcopolymer (Na, K), a salt of vinyl naphthalene-maleic acid copolymer(Na, K), a salt of naphthalene sulfonic acid formalin condensate (Na,K), polyalkylene polyamine, polyacrylamide, polyvinyl pyrrolidone, andpolyethylene glycol.
 2. The dispersion composition according to claim 1,wherein the low molecular weight anionic surfactant and the lowmolecular weight nonionic surfactant have a weight average molecularweight of 100 or more.
 3. The dispersion composition according to claim1, wherein in (C) the polyoxy (ethylene-propylene) block polymers, thecontent of ethylene oxide is from 35 to 90% by weight, and the contentof propylene oxide is from 10 to 65% by weight.
 4. The dispersioncomposition according to claim 1, wherein the (C) polyoxy(ethylene-propylene) block polymers have a weight average molecularweight of from 5,000 to 20,000.